# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222

_publ_contact_author_name        'Prof Dr Miaoli Zhu'
_publ_contact_author_address     
;
Institute of Molecular Science,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
_publ_contact_author_phone       '0086 351 701 7974'
_publ_contact_author_fax         ?
_publ_contact_author_email       miaoli@sxu.edu.cn

#==========================================================================
# TITLE AND AUTHOR LIST

_publ_section_title              
;
Synthesis and evaluation of oxovanadium(IV) complexes
of Schiff-base condensates from 5-substituted-2-hydroxybenzaldehyde
and 2-substituted-benzenamine as selective inhibitors of protein
tyrosine phosphatases
;
_publ_section_title_footnote     
;
?
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address

#<--'Last name, first name'
#<--'Last name, first name'
#<--'Last name, first name'

#<--'Last name, first name'
#<--'Last name, first name'
'Han, Hong'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Lu, Liping'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Wang, Qingming'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Zhu, Miaoli'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;
'Yuan, Caixia'
;
Institute of Molecular Science,
Key Laboratory of Chemical Biology and Molecular
Engineering of the Education Ministry,
Shanxi University,
Taiyuan, Shanxi 030006,
People's Republic of China
;

#==========================================================================
data_VO-BrL
_database_code_depnum_ccdc_archive 'CCDC 862832'
#TrackingRef 'HH63-15_to_CCDC.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Br N O6 V, 1.5(H2 O)'
_chemical_formula_sum            'C14 H15 Br N O7.50 V'
_chemical_formula_weight         448.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
V V 0.3005 0.5294 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.835(4)
_cell_length_b                   7.3740(9)
_cell_length_c                   13.0857(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.497(2)
_cell_angle_gamma                90.00
_cell_volume                     3261.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6213
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.26

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    3.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5762
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17390
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         25.59
_reflns_number_total             3051
_reflns_number_gt                2628
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+5.2556P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3051
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0568
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.425799(10) 0.34555(5) 0.31611(3) 0.02370(10) Uani 1 1 d . . .
N1 N 0.36828(5) 0.2722(3) 0.27191(13) 0.0246(4) Uani 1 1 d . . .
O1 O 0.41986(5) 0.5571(2) 0.30059(12) 0.0377(4) Uani 1 1 d . . .
O2 O 0.41489(4) 0.3172(2) 0.46085(11) 0.0301(4) Uani 1 1 d . . .
O3 O 0.44225(4) 0.2646(2) 0.17970(11) 0.0304(4) Uani 1 1 d . . .
O4 O 0.44052(5) 0.1539(3) 0.02382(13) 0.0407(4) Uani 1 1 d . . .
O5 O 0.48454(5) 0.3693(3) 0.36106(13) 0.0377(4) Uani 1 1 d . . .
H5 H 0.4929(11) 0.477(6) 0.375(3) 0.083(13) Uiso 1 1 d . . .
H5B H 0.5041(10) 0.309(5) 0.345(2) 0.060(10) Uiso 1 1 d . . .
O6 O 0.43488(7) 0.0459(3) 0.33827(17) 0.0431(5) Uani 1 1 d . . .
H6 H 0.4510(10) 0.007(5) 0.307(3) 0.058(11) Uiso 1 1 d . . .
H6B H 0.4354(10) 0.001(5) 0.390(3) 0.057(11) Uiso 1 1 d . . .
Br1 Br 0.269187(8) 0.09253(5) 0.67397(2) 0.05056(11) Uani 1 1 d . . .
C1 C 0.34798(6) 0.2064(3) 0.44591(16) 0.0258(5) Uani 1 1 d . . .
C2 C 0.38279(6) 0.2571(3) 0.50244(16) 0.0256(5) Uani 1 1 d . . .
C3 C 0.38301(7) 0.2420(3) 0.60987(17) 0.0321(5) Uani 1 1 d . . .
H3 H 0.4062 0.2676 0.6480 0.039 Uiso 1 1 calc R . .
C4 C 0.35015(7) 0.1908(3) 0.65939(17) 0.0344(6) Uani 1 1 d . . .
H4 H 0.3508 0.1847 0.7304 0.041 Uiso 1 1 calc R . .
C5 C 0.31579(7) 0.1479(3) 0.60303(18) 0.0326(5) Uani 1 1 d . . .
C6 C 0.31442(7) 0.1522(3) 0.49888(17) 0.0307(5) Uani 1 1 d . . .
H6A H 0.2913 0.1194 0.4625 0.037 Uiso 1 1 calc R . .
C7 C 0.34297(6) 0.2160(3) 0.33624(16) 0.0270(5) Uani 1 1 d . . .
H7 H 0.3187 0.1773 0.3083 0.032 Uiso 1 1 calc R . .
C8 C 0.35481(6) 0.2928(3) 0.16683(16) 0.0254(5) Uani 1 1 d . . .
C9 C 0.31640(7) 0.3516(3) 0.14526(18) 0.0333(5) Uani 1 1 d . . .
H9 H 0.3004 0.3805 0.1989 0.040 Uiso 1 1 calc R . .
C10 C 0.30144(8) 0.3683(4) 0.04576(19) 0.0390(6) Uani 1 1 d . . .
H10 H 0.2755 0.4070 0.0327 0.047 Uiso 1 1 calc R . .
C11 C 0.32525(8) 0.3272(4) -0.03400(18) 0.0387(6) Uani 1 1 d . . .
H11 H 0.3152 0.3344 -0.1012 0.046 Uiso 1 1 calc R . .
C12 C 0.36383(7) 0.2756(3) -0.01400(17) 0.0326(5) Uani 1 1 d . . .
H12 H 0.3798 0.2508 -0.0684 0.039 Uiso 1 1 calc R . .
C13 C 0.37967(6) 0.2595(3) 0.08573(16) 0.0252(5) Uani 1 1 d . . .
C14 C 0.42320(7) 0.2190(3) 0.09641(16) 0.0270(5) Uani 1 1 d . . .
O7 O 0.5000 0.9030(4) 0.2500 0.0424(6) Uani 1 2 d S . .
O8 O 0.51025(7) 0.7016(3) 0.42337(14) 0.0452(5) Uani 1 1 d . . .
H7A H 0.5068(9) 0.836(4) 0.298(2) 0.050(9) Uiso 1 1 d . . .
H8A H 0.4936(11) 0.743(5) 0.457(3) 0.068(12) Uiso 1 1 d . . .
H8B H 0.5350(14) 0.691(6) 0.460(3) 0.116(16) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
V1 0.01962(19) 0.0321(2) 0.01947(18) 0.00028(15) 0.00140(14) -0.00042(15)
N1 0.0212(9) 0.0325(10) 0.0202(9) 0.0001(8) 0.0014(7) 0.0007(8)
O1 0.0416(10) 0.0359(10) 0.0352(9) 0.0027(7) -0.0018(8) -0.0008(8)
O2 0.0254(8) 0.0436(10) 0.0215(8) -0.0016(7) 0.0017(6) -0.0045(7)
O3 0.0213(8) 0.0491(10) 0.0210(8) -0.0020(7) 0.0031(6) 0.0000(7)
O4 0.0316(9) 0.0596(12) 0.0313(9) -0.0155(8) 0.0065(7) 0.0004(8)
O5 0.0204(9) 0.0590(13) 0.0337(9) -0.0072(9) 0.0013(7) -0.0003(9)
O6 0.0576(13) 0.0384(11) 0.0340(11) 0.0075(9) 0.0104(10) 0.0152(10)
Br1 0.03332(16) 0.0789(2) 0.04082(16) 0.01464(14) 0.01728(11) 0.00564(13)
C1 0.0244(11) 0.0306(12) 0.0228(11) -0.0003(9) 0.0037(9) 0.0012(9)
C2 0.0252(11) 0.0277(12) 0.0244(11) -0.0028(9) 0.0057(9) 0.0017(9)
C3 0.0324(13) 0.0401(14) 0.0238(11) -0.0037(10) -0.0005(10) -0.0016(11)
C4 0.0401(14) 0.0419(15) 0.0216(11) 0.0010(10) 0.0069(10) 0.0028(11)
C5 0.0295(12) 0.0371(14) 0.0323(12) 0.0048(10) 0.0138(10) 0.0025(10)
C6 0.0241(11) 0.0382(13) 0.0300(12) 0.0012(10) 0.0036(9) 0.0003(10)
C7 0.0209(11) 0.0339(13) 0.0262(11) -0.0024(9) 0.0001(9) -0.0025(9)
C8 0.0243(11) 0.0285(12) 0.0232(11) 0.0005(9) -0.0012(9) -0.0030(9)
C9 0.0265(12) 0.0437(15) 0.0298(12) 0.0033(11) 0.0021(10) 0.0028(11)
C10 0.0299(13) 0.0483(16) 0.0380(14) 0.0078(12) -0.0075(11) 0.0046(11)
C11 0.0416(15) 0.0476(16) 0.0261(12) 0.0054(11) -0.0081(11) 0.0001(12)
C12 0.0372(13) 0.0377(14) 0.0230(11) 0.0002(10) 0.0017(10) -0.0037(11)
C13 0.0273(12) 0.0262(12) 0.0221(11) -0.0001(9) 0.0005(9) -0.0040(9)
C14 0.0294(12) 0.0292(12) 0.0226(11) 0.0012(9) 0.0039(9) -0.0029(10)
O7 0.0489(17) 0.0481(17) 0.0305(14) 0.000 0.0052(12) 0.000
O8 0.0397(11) 0.0636(14) 0.0317(10) 0.0043(9) -0.0029(9) -0.0053(10)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
V1 O1 1.5849(18) . ?
V1 O2 1.9566(15) . ?
V1 O3 1.9848(15) . ?
V1 O5 2.0555(18) . ?
V1 N1 2.0776(18) . ?
V1 O6 2.248(2) . ?
N1 C7 1.295(3) . ?
N1 C8 1.438(3) . ?
O2 C2 1.313(3) . ?
O3 C14 1.286(3) . ?
O4 C14 1.235(3) . ?
O5 H5 0.86(4) . ?
O5 H5B 0.83(4) . ?
O6 H6 0.75(3) . ?
O6 H6B 0.75(3) . ?
Br1 C5 1.908(2) . ?
C1 C6 1.413(3) . ?
C1 C2 1.414(3) . ?
C1 C7 1.440(3) . ?
C2 C3 1.410(3) . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.362(3) . ?
C6 H6A 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.388(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.503(3) . ?
O7 H7A 0.83(3) . ?
O8 H8A 0.79(4) . ?
O8 H8B 0.95(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 O2 101.59(8) . . ?
O1 V1 O3 102.70(8) . . ?
O2 V1 O3 155.59(7) . . ?
O1 V1 O5 93.92(9) . . ?
O2 V1 O5 87.30(7) . . ?
O3 V1 O5 88.70(7) . . ?
O1 V1 N1 96.25(8) . . ?
O2 V1 N1 91.59(7) . . ?
O3 V1 N1 88.13(7) . . ?
O5 V1 N1 169.79(9) . . ?
O1 V1 O6 179.42(9) . . ?
O2 V1 O6 78.50(8) . . ?
O3 V1 O6 77.18(8) . . ?
O5 V1 O6 85.52(9) . . ?
N1 V1 O6 84.32(8) . . ?
C7 N1 C8 117.67(18) . . ?
C7 N1 V1 122.72(15) . . ?
C8 N1 V1 119.53(13) . . ?
C2 O2 V1 129.17(13) . . ?
C14 O3 V1 133.68(14) . . ?
V1 O5 H5 116(3) . . ?
V1 O5 H5B 131(2) . . ?
H5 O5 H5B 107(3) . . ?
V1 O6 H6 114(3) . . ?
V1 O6 H6B 123(3) . . ?
H6 O6 H6B 109(4) . . ?
C6 C1 C2 119.15(19) . . ?
C6 C1 C7 116.1(2) . . ?
C2 C1 C7 124.6(2) . . ?
O2 C2 C3 118.1(2) . . ?
O2 C2 C1 123.91(19) . . ?
C3 C2 C1 118.0(2) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 Br1 119.93(19) . . ?
C4 C5 Br1 118.80(17) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
N1 C7 C1 127.7(2) . . ?
N1 C7 H7 116.2 . . ?
C1 C7 H7 116.2 . . ?
C9 C8 C13 119.2(2) . . ?
C9 C8 N1 118.9(2) . . ?
C13 C8 N1 121.93(19) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.9(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C8 118.3(2) . . ?
C12 C13 C14 116.04(19) . . ?
C8 C13 C14 125.53(19) . . ?
O4 C14 O3 121.1(2) . . ?
O4 C14 C13 120.1(2) . . ?
O3 C14 C13 118.66(19) . . ?
H8A O8 H8B 112(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 V1 N1 C7 -107.80(19) . . . . ?
O2 V1 N1 C7 -5.95(19) . . . . ?
O3 V1 N1 C7 149.63(19) . . . . ?
O5 V1 N1 C7 77.6(4) . . . . ?
O6 V1 N1 C7 72.32(19) . . . . ?
O1 V1 N1 C8 68.76(17) . . . . ?
O2 V1 N1 C8 170.61(16) . . . . ?
O3 V1 N1 C8 -33.81(16) . . . . ?
O5 V1 N1 C8 -105.8(4) . . . . ?
O6 V1 N1 C8 -111.12(17) . . . . ?
O1 V1 O2 C2 101.84(19) . . . . ?
O3 V1 O2 C2 -83.8(2) . . . . ?
O5 V1 O2 C2 -164.7(2) . . . . ?
N1 V1 O2 C2 5.13(19) . . . . ?
O6 V1 O2 C2 -78.74(19) . . . . ?
O1 V1 O3 C14 -85.2(2) . . . . ?
O2 V1 O3 C14 100.5(2) . . . . ?
O5 V1 O3 C14 -178.9(2) . . . . ?
N1 V1 O3 C14 10.8(2) . . . . ?
O6 V1 O3 C14 95.4(2) . . . . ?
V1 O2 C2 C3 177.15(16) . . . . ?
V1 O2 C2 C1 -2.8(3) . . . . ?
C6 C1 C2 O2 -176.8(2) . . . . ?
C7 C1 C2 O2 -0.8(4) . . . . ?
C6 C1 C2 C3 3.3(3) . . . . ?
C7 C1 C2 C3 179.3(2) . . . . ?
O2 C2 C3 C4 176.1(2) . . . . ?
C1 C2 C3 C4 -3.9(3) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C5 Br1 -175.82(19) . . . . ?
C4 C5 C6 C1 -2.0(4) . . . . ?
Br1 C5 C6 C1 175.22(18) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 -176.8(2) . . . . ?
C8 N1 C7 C1 -171.7(2) . . . . ?
V1 N1 C7 C1 5.0(3) . . . . ?
C6 C1 C7 N1 175.4(2) . . . . ?
C2 C1 C7 N1 -0.7(4) . . . . ?
C7 N1 C8 C9 35.4(3) . . . . ?
V1 N1 C8 C9 -141.33(18) . . . . ?
C7 N1 C8 C13 -146.2(2) . . . . ?
V1 N1 C8 C13 37.0(3) . . . . ?
C13 C8 C9 C10 3.7(4) . . . . ?
N1 C8 C9 C10 -177.9(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C11 C12 C13 C8 1.7(4) . . . . ?
C11 C12 C13 C14 -174.5(2) . . . . ?
C9 C8 C13 C12 -4.2(3) . . . . ?
N1 C8 C13 C12 177.5(2) . . . . ?
C9 C8 C13 C14 171.6(2) . . . . ?
N1 C8 C13 C14 -6.8(3) . . . . ?
V1 O3 C14 O4 -172.05(17) . . . . ?
V1 O3 C14 C13 12.5(3) . . . . ?
C12 C13 C14 O4 -19.8(3) . . . . ?
C8 C13 C14 O4 164.3(2) . . . . ?
C12 C13 C14 O3 155.7(2) . . . . ?
C8 C13 C14 O3 -20.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O8 0.86(4) 1.86(4) 2.714(3) 173(4) . y
O5 H5B O3 0.83(4) 1.88(4) 2.671(2) 156(3) 2_655 y
O6 H6 O7 0.75(3) 2.00(4) 2.743(3) 169(3) 1_545 y
O6 H6B O4 0.75(3) 2.10(4) 2.839(3) 172(4) 6_556 y
O7 H7A O8 0.83(3) 1.91(3) 2.721(3) 166(3) . y
O8 H8A O4 0.79(4) 2.17(4) 2.950(3) 169(3) 6_566 y
O8 H8B O2 0.95(5) 1.95(5) 2.897(3) 177(4) 5_666 y

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.052